The present invention relates to epoxide derivatives of brominated aromatic compounds. More specifically, it relates to ring brominated epoxyaromatic compounds.
It is known to prepare brominated alkyl phenols. See, e g., Can. J. Chem., Vol. 61, pp. 1045-1052 (1983); and Russian Chemical Reviews, Vol. 32, pp. 75-93 (1963). Brominated tetraalkylhydroxyaromatic compounds having 2 aromatic rings also have been prepared in the past. Brominated tetraalkyl biphenols having the benzene rings directly linked have been prepared from tetraalkyl diphenoquinones; see, e.g., U.S. Pat. Nos. 3,929,908; 3,956,403 and 4,058,570. However, when brominating compounds wherein the aromatic rings have an alkylene bridge, the products typically do not have bromine on the aromatic rings. For example, Bradley and Sanders, J. Chem. Soc., Vol. 1962, pp. 480-486 (1962) disclose the reaction of 3,3',5,5'-tetra-t-butylstilbenequinone with HBr to yield .alpha.,.beta.-dibromo-4,4'-dihydroxy-3,3',5,5'-tetra-t-butyldibenzyl. Kharasch and Joshi, J. Org. Chem., Vol. 22, pp. 1435-1438 (1957) disclose the reaction of bromine with 4,4'-methylenebis(2,6-ditertiarybutylphenol) in the presence of acetic acid to give 1-bromo-1,1-bis-(3,5-ditertiarybutyl-4-hydroxyphenyl)methane.
The compound 2,2'-(1,2-ethanediyl)bis(3,5-dibromo-4,6-dimethylphenol) has been prepared by the hydrogenation of 4',5,6',7-tetrabromo-3',5',6,8-tetramethyl-3,4-dihydrospiro(2H-1-benzopyra n-2,1'-[3,5]cyclohexadien)-2'-one; Ann., Vol. 548, pp. 48-77 at page 57 (1939); and by the bromination of 2,2'-(1,2-ethanediyl)bis(4,6-dimethylphenol).
In view of the deficiencies of prior art bromination methods, it would be desirable to have a simple method for the preparation of novel ring brominated polymethylene-bridged di(dialkylhydroxyaromatic) compounds having terminal para hydroxyl moieties. Such a method would be useful in the preparation of novel epoxy derivatives of said compounds.